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This can be a difficult thing to pin down and figure out.
We wont aim on the WHY so much, as we will concentrate on the FIX......if possible.
Something to keep in mind about this issue.....Outlook is a MICROSOFT application, and iCloud is an APPLE application.
Now we all know Apple and Microsoft are competitors, and only work together if there is MASS amounts of money to be made. Hence iCloud for Windows, and Outlook for mac (as examples)
We may come to the conclusion, that there is a bug that has YET to be vetted out, and will render this issue NOT FIXABLE.
With that said, I will do my absolute best, ***** ***** not give up, until I have bonafide proof, that sides on fixable or not.
So......lets do some initial troubleshooting first.
Turn iCloud Calendar, Contacts and Reminders off and back on
Okay, uninstalling and REinstalling is a good troubleshooting step.
But have you done the instructions ABOVE SPECIFICALLY?
Please keep in mind that troubleshooting a problem piece of software can take some time......and an instant solution is rarely the fix.
I ask that we both be patient, and we will get to the bottom of the issue.
I have used Outlook 2016, and i have used icloud for windows.......i chose NOT to use them TOGETHER, because they are made by competitive companies......a different MORE FRIENDLY application is best suited instead of using iCloud. Google Drive comes to mind, and thats just one that works on Apple and Windows machines.
Experience with THIS SPECIFIC issue....NO......but i dont think this particular issue is common, and not many experts WOULD have experience with this issue.
Can i replicate the issue.....not yet.....from my end, the icould and outlook 2016 is working on my computer.
But we dont have the SAME hardware.......thats why i asked what the MAKE and MODEL is of the computer you are using.
correction....that is why i am asking what is the MAKE and MODEL of your computer?
I know you mentioned DELL......do you have a service tag number?
Are all your Windows 10 updates installed? (which shoudl include any updates for MS OFFice and OUtlook2016)
When you UNinstalled icloud, and then REinstalled it.....did you DOWNLOAD the newest version of iCloud for Windows (v5.1)?
If you dont know.....i suggest UNinstalling iCloud, then do a computer RESTART, this will hep REalign the OS again within the RAM.
Then DOWNLOAD the newest iCloud for Windows v5.1 from here:
Then install after you download.
This ensures you have the latest version with all the necessary patches and fixes applied.
Where are you seeing V5.2?
Website shows V5.1
Oh i see it now.
The App shows the verison in the upper R-hand corner
okay....WHERE are you doing the CHECK boxes that WONT stay checked?
Is it Within the OUtlook 2016 program?
Is it within the iCould Program?
is it within the icloud WEBSITE (which uses the Web browser program)
Which is it?
Please take a screen shot......my icloud for windows does NOT have a check box for CONTACTS.
Instead it says to go online to look at and manage contacts and calendar.
See my screen shot:
When you put a check mark in the check box for the CONTACTS......does the APPLY button (at the bottom of the icloud control panel) become available to click?
So, in the image i see the check mark, but the APPLY is greyed out.
Which means that the check mark is ALREADY recognized.
So, you may have to UNcheck the contacts.....then hit apply.
Then check the contacts and hit apply AGAIN.
This is tken RIGHT from the icloud troubleshooting steps.
And we are almost at the END of the list.
The next step is to:
Make sure that the iCloud Outlook Add-in is on
The iCloud Outlook Add-in transfers your content between iCloud and Outlook. Follow these steps to turn on the Add-in:
Open Outlook 2016 and then:
KEEP THIS IN MIND!
Some iCloud features in Outlook work differently than they do on your Apple device. Here are a few tips to help you use Outlook with iCloud for Windows.
Did you check the iCloud Add-On for Outlook?
What was the results?
Sorry.....okay....we are now at the LAST step, for documented troubleshooting, beyond this.......I work on instinct, and MAY need to have acccess to your computer through remote session to continue to troubleshoot.
Last documented step:
Make sure that iCloud isn’t your default account in Data Files.
When iCloud is set as your default account in Data Files, your data won't sync between your devices.
Open Outlook and then do the following:
Thats okay, thats normal.....because you DONT have an icloud email address
The last thing i can think of, would be to just CREATE an icloud Email address, that may purge the icloud issue.
Its a hunch......as most people dont use icloud WITHOUT having the Email address to go with it.
YOu dont have to USE it.....but this might be whats causing the issue.
If that fails to work.....we would need to do a remote session, so i can go through all the settings.
Remember to RESTART the computer when instructed.
We ask folks to do things that may SEEM trivial.....but we have very VERY good reason.....and to explain them all, would take forever.
I think you understand this......but sometimes peope take it upon themself to ignore certain tasks based on fear or indecision, or know how.
The remote session takes this problem OUT OF THE EQUATION, and allows ME to SEE and control the computer directly.
Also.....for contacts to SYNC across ALL computers.....you MUST login to the iCloud control Panel Program, using the SAME icloud ACCOUNT and PASSWORD.
So your wifes computer, and YOUR computer both have icloud App, and you login to only a single icloud account on BOTH computers.
Cant help but think something was missed, or overlooked.
What Program do yo use to VIEW the contacts? Outlook?
okay......and how can you tell its not working?
Have you tried to ADD a contact and see if it syncs across the 2 computers with icloud for windows and OUTLOOK?
Both computers need to have icoud for windows, and both computers need to have outlook with the Add-on for icloud turned on.
Also you need to logged in to the icloud for windows APP using the SAME account on BOTH computers.
I have found some disheartening information across the web, from Microsft Forums to Apple Forums.
The issue here AGAIN, is that icloud is made by APPLE, and outlook is made by MICROSOFT. These are 2 COMPETEING companies, they rarely play well together, and in some cases, accusations of sabotage have been reported. Where by software made to be compatible......is not. And then each company POINTS the finger at each other. Neither taking the blame.....and the problem remains UNFIXED.
YOu may have one of these issues.
Although most of these reports stem back FROM late 2015 to early 2016, a newer version of icloud which was supposed to address this issue among many others, was released (Version 5.2)
But still there are rare useres reporting this......YOU being some of the first.
Here is the Apple forum showing the newest version 5.2 is not syncing with outlook 2016
I am revviewing it now. YOu can too, if you like?
Okay, I think i may have found a possible WORK AROUND, and it IS RELATED to the updates for MS OFFICE outlook
Reverting outlook 2016 BUILD VERSION back to a build that is known to work (16.0.6868.2067), we just might be able to get icoud to sync once again, like normal.
Its a fairly indepth process, and not really advisable for novices, but if you are willing to try, I will give you the instructions.
In a nutshell the process is as follows:
Reverted the last Office update, then reinstalled iCloud and the Outlook sync should work now.
Here is the instructions (FROM MICROSOFT DIRECTLY) to revert outlook (office 2016 CTR) back to a previous build
Please follow the instructions, and please let me KNOW.
Please also take a moment to RATE my performance, or leave a gratuity if you received top service.